Methanol → 1-(Triisopropylsilyl)pyrrole-3-boronic acid

Participants

Reaction Conditions

Reaction Steps

To −78° C. solution of 3-bromo-1-(triisopropylsilyl)-1H-pyrrole (0.619 g, 2.288 mmol) in 10 mL THF was added tert-butyllithium (2.83 mL of 1.7 M in Heptane, 4.80 mmol) dropwise. The reaction mixture was stirring at −78° C. for 45 minutes, then trimethylborate (2.38 g, 22.88 mmol) was added. The reaction was stirred for another 45 minutes at −78° C. To this was then added 0.9 mL methanol and water solution (V/V=1:1) and the reaction was allowed warm to room temperature. The reaction mixture was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo, and used in the next step without further purification.

Provenance & Evidence